Tetrahydrofuran → 5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

HRID 1625166

반응식

HRID 1625166 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[O:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[C@H:18]3[C:19](=[O:23])[N:20]([CH3:22])[CH2:21][C@@H:17]3[C:16]=2[CH:31]=1.[OH-:32].[Na+].[O:34]1CCCC1>>[CH3:22][N:20]1[CH2:21][CH:17]2[CH:18]([C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[O:26][C:15]3[CH:14]=[CH:13][C:12]([Cl:11])=[CH:31][C:16]=32)[CH2:19]1.[CH:18](/[C:19]([OH:23])=[O:34])=[CH:24]/[C:25]([OH:26])=[O:32]

참가 물질

6

반응물 5

HCID 8028Tetrahydrofuran3회HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 58729182(3aS,12bS)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

생성물 1

HCID 119542935-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole maleate

반응 조건

온도
2.5 °C

실험 절차

Aluminum chloride (4.40 g) is added to tetrahydrofuran (100 mL) at 25-30° C. The solution is cooled to 0-5° C. and a solution of lithium aluminum hydride (1.80 g) in tetrahydrofuran (19 mL) is added. The mixture is stirred for 15-30 minutes. A solution of trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (10.0 g) in tetrahydrofuran (200 mL) is added by drops at 0-5° C. and the mixture is maintained for 1 hour. Sodium hydroxide solution (0.6N, 120 mL) is added at 0 to 5° C. The mixture is extracted with ethyl acetate (240 mL) and layers are separated, then the aqueous layer is washed with ethyl acetate (80 mL). The combined organic layer is washed with saturated brine solution (2×160 mL). The organic layer is dried over anhydrous sodium sulfate (10 g) and the solvent from the organic layer is evaporated at 45° C. The obtained residue is dissolved in 1-propanol (30 mL) at 25-30° C. This solution is added to a solution of maleic acid (5.3 g) in 1-propanol (20 mL) at 25-30° C. The mixture is stirred at 25-35° C. for 24 hours and the obtained solid is collected by filtration, washed with 1-propanol (5 mL), and dried under reduced pressure at 46° C., to afford 6.2 g of the title compound. PXRD pattern: complies with a reference pattern of monoclinic polymorph.

후처리

  1. temperaturethe mixture is maintained for 1 hour
  2. extractionThe mixture is extracted with ethyl acetate (240 mL) and layers
  3. customare separated
  4. washthe aqueous layer is washed with ethyl acetate (80 mL)
  5. washThe combined organic layer is washed with saturated brine solution (2×160 mL)
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate (10 g)
  7. customthe solvent from the organic layer is evaporated at 45° C
  8. dissolutionThe obtained residue is dissolved in 1-propanol (30 mL) at 25-30° C
  9. additionThis solution is added to a solution of maleic acid (5.3 g) in 1-propanol (20 mL) at 25-30° C
  10. stirringThe mixture is stirred at 25-35° C. for 24 hours
  11. filtrationthe obtained solid is collected by filtration
  12. washwashed with 1-propanol (5 mL)
  13. customdried under reduced pressure at 46° C.

출처 및 근거

ORD 기록
ord-344d341d0d5d4a61b4dd6ebed69403b0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779161B2

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